4-Phenyl-1,2,4-triazoline-3,5-dione and its pentafluoro analogue are efficient reagents for trapping arene oxides, e.g. benzene oxide-oxepin, affording crystalline adducts that can be quantitatively analysed by HPLC and MS techniques.
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The Mystery of the Benzene-Oxide/Oxepin Equilibrium-Heavy-Atom Tunneling Reversed by Solvent Interactions.
Angew Chem Int Ed Engl
November 2020
Lehrstuhl für Organische Chemie II, Ruhr-Universität Bochum, Universitätsstraße 150, 44801, Bochum, Germany.
The equilibrium between benzene oxide (1) and oxepin (2) is of large importance for understanding the degradation of benzene in biological systems and in the troposphere. Our studies reveal that at cryogenic temperatures, this equilibration is governed by rare heavy-atom tunneling. In solid argon at 3 K, 1 rearranges to 2 via tunneling with a rate constant of approximately 5.
View Article and Find Full Text PDFModeling the formation and reactions of benzene metabolites.
Chem Biol Interact
March 2010
School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne NE1 7RU, UK.
One or more of the muconaldehyde isomers is a putative product of benzene metabolism. As muconaldehydes are highly reactive dienals and potentially mutagenic they might be relevant to the carcinogenicity of benzene. Muconaldehydes may be derived through the action of a cytochrome P450 mono-oxygenase on benzene oxide-oxepin, which are established metabolites of benzene.
View Article and Find Full Text PDFEvidence from mechanistic probes for distinct hydroperoxide rearrangement mechanisms in the intradiol and extradiol catechol dioxygenases.
J Am Chem Soc
August 2008
Department of Chemistry, University of Warwick, Coventry CV4 7AL, UK.
Three mechanistic probes were used to investigate whether the Criegee rearrangement step of catechol 1,2-dioxygenase (CatA) from Acinetobacter sp. proceeds via a direct 1,2-acyl migration, via homolytic O-O cleavage, or via a benzene oxide-oxepin rearrangement. Incubation of CatA with 3-chloroperoxybenzoic acid led to the formation of a 9:1 mixture of 2-chlorophenol and 3-chlorophenol, via a mechanism involving O-O homolytic cleavage.
View Article and Find Full Text PDFTheoretical reinvestigation of the O(3P) + C6H6 reaction: quantum chemical and statistical rate calculations.
J Phys Chem A
May 2007
Department of Chemistry, University of Leuven, Celestijnenlaan 200F, B-3001, Leuven, Belgium.
The lowest-lying triplet and singlet potential energy surfaces for the O(3P) + C6H6 reaction were theoretically characterized using the "complete basis set" CBS-QB3 model chemistry. The primary product distributions for the multistate multiwell reactions on the individual surfaces were then determined by RRKM statistical rate theory and weak-collision master equation analysis using the exact stochastic simulation method. It is newly found that electrophilic O-addition onto a carbon atom in benzene can occur in parallel on two triplet surfaces, 3A' and 3A' '; the results predict O-addition to be dominant up to combustion temperatures.
View Article and Find Full Text PDFReactions of benzene oxide with thiols including glutathione.
Chem Res Toxicol
February 2005
School of Natural Sciences--Chemistry, Bedson Building, University of Newcastle upon Tyne, Newcastle upon Tyne, NEI 7RU, United Kingdom.
S-Phenylmercapturic acid is a minor metabolite of benzene used as a biomarker for human benzene exposures. The reaction of intracellular glutathione with benzene oxide-oxepin, the initial metabolite of benzene, is presumed to give 1-(S-glutathionyl)-cyclohexa-3,5-dien-2-ol, which undergoes dehydration to S-phenylglutathione, the precursor of S-phenylmercapturic acid. To validate the proposed route to S-phenylglutathione, reactions of benzene oxide-oxepin with glutathione and other sulfur nucleophiles have been studied.
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